Imidazol-4-one-5-propionic acid is an intermediate in the metabolism of

histidine Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the ...

. It is a colorless compound that is sensitive to light in air. The compound features an imidazolone ring.

Occurrence

It arises via the action of

urocanase Urocanase (also known as imidazolonepropionate hydrolase or urocanate hydratase) is the enzyme () that catalyzes the second step in the degradation of histidine, the hydration of urocanate into imidazolonepropionate. Urocanase is coded for by the ...

on urocanic acid. Hydrolysis of the

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

to the glutamic acid derivative is catalyzed by imidazolonepropionate hydrolase. Microbial production of imidazol-4-one-5-propionic acid in the human gut has been shown to affect insulin signaling, which is relevant to

type II diabetes Type 2 diabetes, formerly known as adult-onset diabetes, is a form of diabetes mellitus that is characterized by high blood sugar, insulin resistance, and relative lack of insulin. Common symptoms include increased thirst, frequent urination, ...

References

Carboxylic acids Imidazolines Lactams {{heterocyclic-stub

Occurrence

See also

References